Vacation rentals in Oconomowoc

Lace & Woods Farm "Hammer Hideaway"

HEATED POOL MAY-SEPT FOR ADDITIONAL CHRG. Cozy designer custom built guest house nestled amongst a 10 acre hobby farm. come for a relaxing getaway. This home is an artistic gem! Boasting an open concept, with a queen bed on main level and twin mattress underneath , a full kitchen, cozy living area, wood burning fireplace. The loft has extra sleeping with a double bed and twin bed.Custom designed. Great location winter and summer, enjoy snowmobiling trails and skiing near by or beaches & hiking

Black Squirrel Farmhouse - (Downtown Oconomowoc)

Downtown Oconomowoc, beach, bandshell, bars, shops, restaurants, lakes, kayak/boat rental, 2 public golf courses in town and 3 more within 10 minute drive, 31 parks including the imagination station million dollar play area!!! Lots of local hiking and bike trails through the kettle moraine, visit Lapham peak, government hill, scuppernong, and much more! Minutes to Holy Hill, from the tower you can see the beautiful Lake Country area for miles. Only 1.25 hr drive to the Devils lake state park!

Cozy cottage in the heart of Lake Country

Entire cottage in the heart of Lake Country. Merryhill Cottage is nestled on two acres with mature trees. Included on the two acres- the host's farmhouse, a guest house and barn. The feeling of a country setting but with easy access to Hwys 16, 83 and I 94. Close to shopping, restaurants, parks, hiking, cross country skiing and snowshoeing, lakes, and beaches (10 min. to Delafield and Oconomowoc and 15 min. to Pewaukee.) Perfect for day trips to Madison (54 min.) and Milwaukee (30 min.).

Beautiful Victorian in Historic District

My Victorian home, "Belle Maison" (beautiful house), is waiting just for you. Newly restored, with 2 bedrooms, 2 baths - one with its original claw foot tub!- and a queen size sofa bed in the TV room. It is located in historic, downtown Watertown. Just a block from Main Street - with lots of shops and restaurants within walking distance - and the beautiful Rock River. The location is perfect - whether you're visiting Jefferson County or looking for a home base between Madison and Milwaukee.

Cozy 2BR charm | Big Yard, Fire pit, Replenishing!

Cozy gem sleeps up to 5. Renovated Interiors w/ large balcony overlooking serene yard. Enjoy an eastern sunrise during your morning coffee, or a starry night next to the warmth of a fire. 1 mile from 94 - 20 minutes from Milwaukee. Fully stocked kitchenette. Gas burning stove/oven, microwave, coffee maker, full size fridge/freezer, in unit washer/dryer, wifi, smart tv, wireless printer, private large balcony w/ heater for cooler nights. Perfect space for a couple or traveling profesional.

Charming, Updated and Historic

This is truly a memorable, charming, and welcoming place to stay. You will have the home to yourself. You will love the warm feel, woodwork, and historical prominence of this home. It is very charming throughout and is on a large 1.5-acre estate size lot. The price quoted here is for 1-2 people and a 1 Bedroom suite with 1.5 Baths. Under this listing we can open up to three suites and accept six guests. If need more there than 2 guests and 1 suite we are happy to make you a custom offer.

The Loft @ The Butler Place. 1846 homestead.

The Loft at the Butler Place is a beautiful, quiet retreat set in the rural suburb of Sussex, just 30 minutes west of Milwaukee. The home is the 1846 homestead of the William Butler family, making the home older than the State of Wisconsin! The 2019 remodel of the Loft is in sophisticated farmhouse style and pays tribute to the history of the home in its furnishings, up cycled pieces, and beautiful setting. "Broken becomes blessed" both tells and compells as an invitation to all.

Garden Retreat in law Suite

Welcome to our in-law suite apartment featuring a full eat-in kitchen, living room, queen bed in large bedroom, walk in closet and full bathroom with walk-in shower. Our beautiful two acre yard has many areas to relax in, including a hammock and fire pit for the evenings. Twenty mins. to Erin Hills and Holy Hill and a half hour to most downtown Milwaukee attractions, as well as the RNC activities taking place this summer. Lots of city tips and suggestions for our guests.

Quiet Lake Country Retreat

Charming single family home located in the Village of Oconomowoc Lake. Well appointed for longs stays or perfect for a weekend retreat. Easy access to I94 and Hwy. 16. Minutes away from Olympia Resort, stores, restaurants, downtown Oconomowoc. 10 minute drive to Delafield. 20 minute drive to Erin Hills, site of the 2017 US Open. 35 minutes to downtown Milwaukee. 45 minutes to Madison. *** Coming fall 2024 the back patio will be completely renovated.